(2,4-Dimethyl-1,3-thiazol-5-yl)boronic acid → HCID 58109278, compound

HRID 1046112Notes

Reaction equation

HRID 1046112 reaction equation
[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH3:27][C:28]1[S:29][C:30](B(O)O)=[C:31]([CH3:33])[N:32]=1>>[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:30]3[S:29][C:28]([CH3:27])=[N:32][C:31]=3[CH3:33])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 53420344(2,4-Dimethyl-1,3-thiazol-5-yl)boronic acidHCID 53473487(R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one

Product 1

HCID 58109278HCID 58109278, compound

Procedure

The title compound was prepared from (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one and 2,4-dimethylthiazole-5-boronic acid following a procedure analogous to that described in Example 14. LC-MS Method 1 tR=1.82, min, m/z=451; 1H NMR (CDCl3) 7.26 (t, 2H), 7.13 (d, 2H), 7.03 (t, 2H), 6.91 (d, 2H), 5.76-5.64 (m, 2H), 5.06 (dd, 2H), 2.98 (m, 1H), 2.74 (s, 3H), 2.42 (s, 3H), 1.53 (d, 3H).

Sources & evidence

ORD record
ord-8ff2d3dc9524477580204d04700392e9
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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